Potassium Carbonate → 5-Ethynylpyridin-2-amine

HRID 1984642Notes

Reaction equation

HRID 1984642 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 224828585-(2-(Trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 219548275-Ethynylpyridin-2-amineYield 73.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-trimethylsilanylethynyl-pyridin-2-ylamine (32.1 g, 169 mmol) in THF (150 mL) and methanol (350 mL) at 0° C. was added potassium carbonate (2.33 g, 16.9 mmol) and the mixture was stirred at 0° C. for 5 h. It was diluted with ice water (500 mL), extracted with tert-butylmethylether (3×500 mL), washed the combined organic layers with brine and dried over magnesium sulfate. Concentration left a dark brown solid, which was dissolved in hot ethyl acetate and precipitated with n-heptane trituration to give the 5-ethynyl-pyridin-2-ylamine (14.61 g, 73%) as a light brown solid. MS: m/e=118.1 [M+H]+.

Workup

  1. extractionextracted with tert-butylmethylether (3×500 mL)
  2. washwashed the combined organic layers with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration
  5. waitleft a dark brown solid, which
  6. dissolutionwas dissolved in hot ethyl acetate
  7. customprecipitated with n-heptane trituration

Sources & evidence

ORD record
ord-6301bcd4357a42ee8b09d5abaf9cf50c
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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